DE3438189A1 - Verfahren zur herstellung aromatisch substituierter l-aminosaeuren - Google Patents
Verfahren zur herstellung aromatisch substituierter l-aminosaeurenInfo
- Publication number
- DE3438189A1 DE3438189A1 DE19843438189 DE3438189A DE3438189A1 DE 3438189 A1 DE3438189 A1 DE 3438189A1 DE 19843438189 DE19843438189 DE 19843438189 DE 3438189 A DE3438189 A DE 3438189A DE 3438189 A1 DE3438189 A1 DE 3438189A1
- Authority
- DE
- Germany
- Prior art keywords
- ester
- extracted
- amino acid
- amino acids
- extraction
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- 150000008575 L-amino acids Chemical class 0.000 title claims abstract description 16
- 238000004519 manufacturing process Methods 0.000 title description 3
- 150000002148 esters Chemical class 0.000 claims abstract description 21
- 238000000034 method Methods 0.000 claims abstract description 17
- 238000000605 extraction Methods 0.000 claims abstract description 13
- 238000003776 cleavage reaction Methods 0.000 claims abstract description 10
- 230000007017 scission Effects 0.000 claims abstract description 10
- 230000002255 enzymatic effect Effects 0.000 claims abstract description 9
- 150000008574 D-amino acids Chemical class 0.000 claims abstract description 8
- 108010027597 alpha-chymotrypsin Proteins 0.000 claims abstract description 5
- 239000003960 organic solvent Substances 0.000 claims abstract description 5
- 239000011541 reaction mixture Substances 0.000 claims abstract description 3
- 239000012670 alkaline solution Substances 0.000 claims abstract 4
- 238000002360 preparation method Methods 0.000 claims abstract 2
- 230000006340 racemization Effects 0.000 claims description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 12
- 239000000284 extract Substances 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 7
- CFYIUBWVKZQDOG-UHFFFAOYSA-N 4-[[2-[[2-[[1-(4-nitroanilino)-1-oxo-3-phenylpropan-2-yl]amino]-2-oxoethyl]amino]-2-oxoethyl]amino]-4-oxobutanoic acid Chemical compound C=1C=C([N+]([O-])=O)C=CC=1NC(=O)C(NC(=O)CNC(=O)CNC(=O)CCC(=O)O)CC1=CC=CC=C1 CFYIUBWVKZQDOG-UHFFFAOYSA-N 0.000 claims description 4
- 230000002378 acidificating effect Effects 0.000 claims description 4
- -1 allyl ester Chemical class 0.000 claims description 4
- 239000002253 acid Substances 0.000 abstract description 10
- 125000005907 alkyl ester group Chemical group 0.000 abstract description 2
- 239000000243 solution Substances 0.000 description 21
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 229960005190 phenylalanine Drugs 0.000 description 9
- QIVBCDIJIAJPQS-VIFPVBQESA-N L-tryptophane Chemical compound C1=CC=C2C(C[C@H](N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-VIFPVBQESA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 description 7
- 108090000790 Enzymes Proteins 0.000 description 6
- 102000004190 Enzymes Human genes 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 6
- 229940088598 enzyme Drugs 0.000 description 6
- 235000008729 phenylalanine Nutrition 0.000 description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
- 229960004799 tryptophan Drugs 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 229940024606 amino acid Drugs 0.000 description 4
- 235000001014 amino acid Nutrition 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 239000008367 deionised water Substances 0.000 description 4
- 229910021641 deionized water Inorganic materials 0.000 description 4
- 238000004128 high performance liquid chromatography Methods 0.000 description 4
- 150000002576 ketones Chemical class 0.000 description 4
- 230000003287 optical effect Effects 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 3
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 150000001413 amino acids Chemical class 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 230000020477 pH reduction Effects 0.000 description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- QIVBCDIJIAJPQS-UHFFFAOYSA-N Tryptophan Natural products C1=CC=C2C(CC(N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-UHFFFAOYSA-N 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 125000000468 ketone group Chemical group 0.000 description 2
- VSDUZFOSJDMAFZ-SECBINFHSA-N methyl (2r)-2-amino-3-phenylpropanoate Chemical compound COC(=O)[C@H](N)CC1=CC=CC=C1 VSDUZFOSJDMAFZ-SECBINFHSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- SMQUZDBALVYZAC-UHFFFAOYSA-N salicylaldehyde Chemical compound OC1=CC=CC=C1C=O SMQUZDBALVYZAC-UHFFFAOYSA-N 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 238000001291 vacuum drying Methods 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- 108090000317 Chymotrypsin Proteins 0.000 description 1
- 229930182827 D-tryptophan Natural products 0.000 description 1
- QIVBCDIJIAJPQS-SECBINFHSA-N D-tryptophane Chemical compound C1=CC=C2C(C[C@@H](N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-SECBINFHSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- SXRSQZLOMIGNAQ-UHFFFAOYSA-N Glutaraldehyde Chemical compound O=CCCCC=O SXRSQZLOMIGNAQ-UHFFFAOYSA-N 0.000 description 1
- OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 description 1
- 206010035148 Plague Diseases 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- YKTSYUJCYHOUJP-UHFFFAOYSA-N [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] Chemical compound [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] YKTSYUJCYHOUJP-UHFFFAOYSA-N 0.000 description 1
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 229960002376 chymotrypsin Drugs 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229960004502 levodopa Drugs 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- SWVMLNPDTIFDDY-FVGYRXGTSA-N methyl (2s)-2-amino-3-phenylpropanoate;hydrochloride Chemical compound Cl.COC(=O)[C@@H](N)CC1=CC=CC=C1 SWVMLNPDTIFDDY-FVGYRXGTSA-N 0.000 description 1
- KCUNTYMNJVXYKZ-UHFFFAOYSA-N methyl 2-amino-3-(1h-indol-3-yl)propanoate Chemical compound C1=CC=C2C(CC(N)C(=O)OC)=CNC2=C1 KCUNTYMNJVXYKZ-UHFFFAOYSA-N 0.000 description 1
- VSDUZFOSJDMAFZ-UHFFFAOYSA-N methyl 2-amino-3-phenylpropanoate Chemical compound COC(=O)C(N)CC1=CC=CC=C1 VSDUZFOSJDMAFZ-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 150000002994 phenylalanines Chemical class 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 239000008055 phosphate buffer solution Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- UDHATSFDZHRLJT-UHFFFAOYSA-N propan-2-one;3-triethoxysilylpropan-1-amine Chemical compound CC(C)=O.CCO[Si](OCC)(OCC)CCCN UDHATSFDZHRLJT-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 150000003839 salts Chemical group 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P13/00—Preparation of nitrogen-containing organic compounds
- C12P13/04—Alpha- or beta- amino acids
- C12P13/22—Tryptophan; Tyrosine; Phenylalanine; 3,4-Dihydroxyphenylalanine
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P41/00—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture
- C12P41/003—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture by ester formation, lactone formation or the inverse reactions
- C12P41/005—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture by ester formation, lactone formation or the inverse reactions by esterification of carboxylic acid groups in the enantiomers or the inverse reaction
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Zoology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Wood Science & Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Genetics & Genomics (AREA)
- General Chemical & Material Sciences (AREA)
- Biotechnology (AREA)
- Microbiology (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Analytical Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Priority Applications (16)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19843438189 DE3438189A1 (de) | 1984-10-18 | 1984-10-18 | Verfahren zur herstellung aromatisch substituierter l-aminosaeuren |
| DE8585112563T DE3579663D1 (de) | 1984-10-18 | 1985-10-04 | Verfahren zur herstellung aromatisch substituierter l-aminosaeuren. |
| EP85112563A EP0178553B1 (de) | 1984-10-18 | 1985-10-04 | Verfahren zur Herstellung aromatisch substituierter L-Aminosäuren |
| AT85112563T ATE56472T1 (de) | 1984-10-18 | 1985-10-04 | Verfahren zur herstellung aromatisch substituierter l-aminosaeuren. |
| HU853963A HUT39414A (en) | 1984-10-18 | 1985-10-14 | Process for preparing aromatic l-aminoacids |
| GR852491A GR852491B (cs) | 1984-10-18 | 1985-10-15 | |
| CS857385A CS258132B2 (en) | 1984-10-18 | 1985-10-16 | Method of l-phenylalanine and l-tryphtofan production |
| FI854025A FI854025A7 (fi) | 1984-10-18 | 1985-10-16 | Menetelmä aromaattisesti substituoitujen L-aminohappojen valmistamiseksi. |
| ES547901A ES8609186A1 (es) | 1984-10-18 | 1985-10-16 | Procedimiento para preparar l-aminoacidos aromaticamente sustituidos |
| ZA857971A ZA857971B (en) | 1984-10-18 | 1985-10-17 | A process for the preparation of aromatically substituted l-amino acids |
| CA000493202A CA1265083A (en) | 1984-10-18 | 1985-10-17 | Process for the preparation of aromatically substituted l-amino acids |
| JP60230056A JPS61108398A (ja) | 1984-10-18 | 1985-10-17 | 芳香族置換されたｌ‐アミノ酸の製法 |
| DK475585A DK475585A (da) | 1984-10-18 | 1985-10-17 | Fremgangsmaade til fremstilling af aromatisk substituerede l-aminosyrer |
| NO854127A NO854127L (no) | 1984-10-18 | 1985-10-17 | Fremgangsm¨te til fremstilling av aromatisk substituerte l -aminosyrer. |
| PT81320A PT81320B (de) | 1984-10-18 | 1985-10-17 | Verfahren zur herstellung aromatisch substituierter l-aminosauren |
| IL76740A IL76740A0 (en) | 1984-10-18 | 1985-10-17 | Process for the preparation of aromatically substituted l-amino acids |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19843438189 DE3438189A1 (de) | 1984-10-18 | 1984-10-18 | Verfahren zur herstellung aromatisch substituierter l-aminosaeuren |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE3438189A1 true DE3438189A1 (de) | 1986-04-24 |
Family
ID=6248201
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19843438189 Withdrawn DE3438189A1 (de) | 1984-10-18 | 1984-10-18 | Verfahren zur herstellung aromatisch substituierter l-aminosaeuren |
| DE8585112563T Expired - Fee Related DE3579663D1 (de) | 1984-10-18 | 1985-10-04 | Verfahren zur herstellung aromatisch substituierter l-aminosaeuren. |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE8585112563T Expired - Fee Related DE3579663D1 (de) | 1984-10-18 | 1985-10-04 | Verfahren zur herstellung aromatisch substituierter l-aminosaeuren. |
Country Status (15)
| Country | Link |
|---|---|
| EP (1) | EP0178553B1 (cs) |
| JP (1) | JPS61108398A (cs) |
| AT (1) | ATE56472T1 (cs) |
| CA (1) | CA1265083A (cs) |
| CS (1) | CS258132B2 (cs) |
| DE (2) | DE3438189A1 (cs) |
| DK (1) | DK475585A (cs) |
| ES (1) | ES8609186A1 (cs) |
| FI (1) | FI854025A7 (cs) |
| GR (1) | GR852491B (cs) |
| HU (1) | HUT39414A (cs) |
| IL (1) | IL76740A0 (cs) |
| NO (1) | NO854127L (cs) |
| PT (1) | PT81320B (cs) |
| ZA (1) | ZA857971B (cs) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3618465A1 (de) * | 1986-06-02 | 1987-12-03 | Hoechst Ag | Durchfuehrung von biokatalysatorreaktionen in einem wirbelbettreaktor mit fluessigem 2-phasen-system |
| DE3622662A1 (de) * | 1986-07-05 | 1988-01-14 | Hoechst Ag | Verfahren zur kontinuierlichen biokatalytischen umsetzung von substraten, die in waessrigen loesungen schwer loeslich sind |
| US5002871A (en) * | 1986-08-18 | 1991-03-26 | The Coca-Cola Company | Enzymatic membrane method for the synthesis and separation of peptides |
| DE3839379A1 (de) * | 1988-11-22 | 1990-05-23 | Hoechst Ag | Verfahren zur herstellung von tripeptiden |
| US5025325A (en) * | 1989-10-13 | 1991-06-18 | Hewlett-Packard Company | Graphics scaling method for high resolution printers |
| DE19546532C2 (de) * | 1995-12-13 | 2000-04-20 | Degussa | Verfahren zur Gewinnung von optisch aktiven L-alpha-Aminocarbonsäuren aus entsprechenden racemischen D,L-alpha-Aminocarbonsäuren |
| FR2778671B1 (fr) | 1998-05-14 | 2002-07-05 | Rhone Poulenc Agrochimie | Nouveau procede de preparation d'intermediaires de synthese |
| HU228360B1 (en) | 2001-09-25 | 2013-03-28 | Hoffmann La Roche | Enzymatic process for the preparation of substituted 2-amino-3-(2-amino-phenylsulfanyl)-propionic acid |
| JP5028672B2 (ja) * | 2007-05-23 | 2012-09-19 | ボイス パテント ゲーエムベーハー | 古紙裁断用ロータ |
| JP4934881B2 (ja) * | 2007-05-23 | 2012-05-23 | ボイス パテント ゲーエムベーハー | 古紙裁断用ロータ |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA947214A (en) * | 1971-04-02 | 1974-05-14 | Antoine D'iorio | Resolution of racemates of ring-substituted phenylalanines |
| US3878043A (en) * | 1973-01-02 | 1975-04-15 | Univ Southern Illinois | Method for preparing L-dopa and novels compounds useful therein |
-
1984
- 1984-10-18 DE DE19843438189 patent/DE3438189A1/de not_active Withdrawn
-
1985
- 1985-10-04 EP EP85112563A patent/EP0178553B1/de not_active Expired - Lifetime
- 1985-10-04 AT AT85112563T patent/ATE56472T1/de not_active IP Right Cessation
- 1985-10-04 DE DE8585112563T patent/DE3579663D1/de not_active Expired - Fee Related
- 1985-10-14 HU HU853963A patent/HUT39414A/hu unknown
- 1985-10-15 GR GR852491A patent/GR852491B/el unknown
- 1985-10-16 CS CS857385A patent/CS258132B2/cs unknown
- 1985-10-16 ES ES547901A patent/ES8609186A1/es not_active Expired
- 1985-10-16 FI FI854025A patent/FI854025A7/fi not_active Application Discontinuation
- 1985-10-17 NO NO854127A patent/NO854127L/no unknown
- 1985-10-17 JP JP60230056A patent/JPS61108398A/ja active Pending
- 1985-10-17 PT PT81320A patent/PT81320B/pt unknown
- 1985-10-17 CA CA000493202A patent/CA1265083A/en not_active Expired - Fee Related
- 1985-10-17 IL IL76740A patent/IL76740A0/xx unknown
- 1985-10-17 DK DK475585A patent/DK475585A/da not_active Application Discontinuation
- 1985-10-17 ZA ZA857971A patent/ZA857971B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ATE56472T1 (de) | 1990-09-15 |
| ES8609186A1 (es) | 1986-09-01 |
| CA1265083A (en) | 1990-01-30 |
| PT81320A (de) | 1985-11-01 |
| ZA857971B (en) | 1986-05-28 |
| EP0178553A2 (de) | 1986-04-23 |
| DK475585D0 (da) | 1985-10-17 |
| DK475585A (da) | 1986-04-19 |
| CS258132B2 (en) | 1988-07-15 |
| FI854025A0 (fi) | 1985-10-16 |
| PT81320B (de) | 1987-05-18 |
| FI854025L (fi) | 1986-04-19 |
| IL76740A0 (en) | 1986-02-28 |
| FI854025A7 (fi) | 1986-04-19 |
| EP0178553A3 (en) | 1987-04-29 |
| NO854127L (no) | 1986-04-21 |
| DE3579663D1 (de) | 1990-10-18 |
| ES547901A0 (es) | 1986-09-01 |
| JPS61108398A (ja) | 1986-05-27 |
| EP0178553B1 (de) | 1990-09-12 |
| HUT39414A (en) | 1986-09-29 |
| CS738585A2 (en) | 1987-12-17 |
| GR852491B (cs) | 1986-02-11 |
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